Careless represents the culmination of years of work, preparation, and growth. Meticulously recorded over three years in Upstate New York and Buenos Aires, Argentina, Careless might be an anachronism: at a time when the very idea of the record-album is called into question—when technological developments and listening habits challenge its status as the natural vehicle of an artist's presentation of new material—Shindell offers us an ambitious, luxurious, full-length statement. Accompanied by his co-producer Greg Anderson, engineer/arranger Scott Petito, and a group of A-list musicians, Shindell immersed himself in the studio, allowing the time and latitude to explore, experiment, take risks—to play—as each of these eleven songs was given form and substance. While his signature acoustic guitar style is used to good effect here, Careless finds Shindell plugging in more. "Returning to the electric guitar has transformed my relationship with all aspects of my career," he says. "The wider sonic and dynamic range of the electric has been a real inspiration. Rejuvenating.”

Careless exhibits a wide thematic range, from terrestrial to celestial. It begins with seven songs whose feet are very much on the ground: the roots-of-rock’n’roll lope and twang of Stray Cow Blues; the epic mea culpa and pop catharsis of the title track; desire both human and insect in the “summer garden” of Infrared; the ruminant, dystopian, blues-grazing Deer on the Parkway; recovery and reconciliation between a father and daughter, in All Wide Open; a vintage instrument infused with the spirit of a prior owner in Your Guitar; and Abbie, wherein the disappearance of a beloved pet is explained. And from there to the view from above: the ether of Atlas Choking, heaven itself in Before You Go, and geosynchronous orbit in Satellites. With its only cover, The Dome, the album ends where it began: firmly on the ground, beneath a night sky, wondering, awaiting clarification.